EP1123358A1 - Dispersions a stabilite amelioree - Google Patents
Dispersions a stabilite amelioreeInfo
- Publication number
- EP1123358A1 EP1123358A1 EP99950192A EP99950192A EP1123358A1 EP 1123358 A1 EP1123358 A1 EP 1123358A1 EP 99950192 A EP99950192 A EP 99950192A EP 99950192 A EP99950192 A EP 99950192A EP 1123358 A1 EP1123358 A1 EP 1123358A1
- Authority
- EP
- European Patent Office
- Prior art keywords
- dispersion
- cross
- insoluble
- liquid vehicle
- particles
- Prior art date
- Legal status (The legal status is an assumption and is not a legal conclusion. Google has not performed a legal analysis and makes no representation as to the accuracy of the status listed.)
- Granted
Links
- 239000006185 dispersion Substances 0.000 title claims abstract description 100
- 239000002245 particle Substances 0.000 claims abstract description 61
- 229920000642 polymer Polymers 0.000 claims abstract description 52
- 239000007788 liquid Substances 0.000 claims abstract description 50
- 238000004132 cross linking Methods 0.000 claims abstract description 31
- 239000002270 dispersing agent Substances 0.000 claims abstract description 28
- 239000000178 monomer Substances 0.000 claims abstract description 25
- 238000005538 encapsulation Methods 0.000 claims abstract description 10
- 239000000049 pigment Substances 0.000 claims description 36
- XLYOFNOQVPJJNP-UHFFFAOYSA-N water Substances O XLYOFNOQVPJJNP-UHFFFAOYSA-N 0.000 claims description 23
- 239000003054 catalyst Substances 0.000 claims description 13
- 125000002887 hydroxy group Chemical group [H]O* 0.000 claims description 7
- 150000001412 amines Chemical group 0.000 claims description 6
- 239000003960 organic solvent Substances 0.000 claims description 6
- 239000002253 acid Chemical group 0.000 claims description 5
- UKLDJPRMSDWDSL-UHFFFAOYSA-L [dibutyl(dodecanoyloxy)stannyl] dodecanoate Chemical compound CCCCCCCCCCCC(=O)O[Sn](CCCC)(CCCC)OC(=O)CCCCCCCCCCC UKLDJPRMSDWDSL-UHFFFAOYSA-L 0.000 claims description 4
- 239000004593 Epoxy Substances 0.000 claims description 2
- BLRPTPMANUNPDV-UHFFFAOYSA-N Silane Chemical compound [SiH4] BLRPTPMANUNPDV-UHFFFAOYSA-N 0.000 claims description 2
- 239000012975 dibutyltin dilaurate Substances 0.000 claims description 2
- VFFDVELHRCMPLY-UHFFFAOYSA-N dimethyldodecyl amine Natural products CC(C)CCCCCCCCCCCN VFFDVELHRCMPLY-UHFFFAOYSA-N 0.000 claims description 2
- 239000012948 isocyanate Substances 0.000 claims description 2
- 150000002513 isocyanates Chemical class 0.000 claims description 2
- YWFWDNVOPHGWMX-UHFFFAOYSA-N n,n-dimethyldodecan-1-amine Chemical compound CCCCCCCCCCCCN(C)C YWFWDNVOPHGWMX-UHFFFAOYSA-N 0.000 claims description 2
- XTAZYLNFDRKIHJ-UHFFFAOYSA-N n,n-dioctyloctan-1-amine Chemical compound CCCCCCCCN(CCCCCCCC)CCCCCCCC XTAZYLNFDRKIHJ-UHFFFAOYSA-N 0.000 claims description 2
- IMFACGCPASFAPR-UHFFFAOYSA-N tributylamine Chemical compound CCCCN(CCCC)CCCC IMFACGCPASFAPR-UHFFFAOYSA-N 0.000 claims description 2
- SWZDQOUHBYYPJD-UHFFFAOYSA-N tridodecylamine Chemical compound CCCCCCCCCCCCN(CCCCCCCCCCCC)CCCCCCCCCCCC SWZDQOUHBYYPJD-UHFFFAOYSA-N 0.000 claims description 2
- 125000003903 2-propenyl group Chemical group [H]C([*])([H])C([H])=C([H])[H] 0.000 claims 2
- 150000008064 anhydrides Chemical group 0.000 claims 2
- 125000002485 formyl group Chemical class [H]C(*)=O 0.000 claims 2
- BPQQTUXANYXVAA-UHFFFAOYSA-N Orthosilicate Chemical compound [O-][Si]([O-])([O-])[O-] BPQQTUXANYXVAA-UHFFFAOYSA-N 0.000 claims 1
- 150000005676 cyclic carbonates Chemical class 0.000 claims 1
- 150000002118 epoxides Chemical class 0.000 claims 1
- 150000002148 esters Chemical class 0.000 claims 1
- XLYOFNOQVPJJNP-UHFFFAOYSA-M hydroxide Chemical compound [OH-] XLYOFNOQVPJJNP-UHFFFAOYSA-M 0.000 claims 1
- 150000002466 imines Chemical class 0.000 claims 1
- 239000003999 initiator Substances 0.000 claims 1
- KFUUVTXGQZYOIO-UHFFFAOYSA-N isocyanato 3-oxobutanoate Chemical compound C(CC(=O)C)(=O)ON=C=O KFUUVTXGQZYOIO-UHFFFAOYSA-N 0.000 claims 1
- ISWSIDIOOBJBQZ-UHFFFAOYSA-N phenol group Chemical group C1(=CC=CC=C1)O ISWSIDIOOBJBQZ-UHFFFAOYSA-N 0.000 claims 1
- 229920001296 polysiloxane Polymers 0.000 claims 1
- 150000003254 radicals Chemical class 0.000 claims 1
- 229910000077 silane Inorganic materials 0.000 claims 1
- SCPYDCQAZCOKTP-UHFFFAOYSA-N silanol Chemical compound [SiH3]O SCPYDCQAZCOKTP-UHFFFAOYSA-N 0.000 claims 1
- 239000000203 mixture Substances 0.000 abstract description 28
- 239000000976 ink Substances 0.000 abstract description 26
- 150000001875 compounds Chemical class 0.000 abstract description 11
- 239000003973 paint Substances 0.000 abstract description 8
- 238000000576 coating method Methods 0.000 abstract description 7
- 239000011248 coating agent Substances 0.000 abstract description 3
- 238000007639 printing Methods 0.000 abstract description 2
- 239000010954 inorganic particle Substances 0.000 abstract 1
- 239000011146 organic particle Substances 0.000 abstract 1
- 239000003981 vehicle Substances 0.000 description 37
- 238000006243 chemical reaction Methods 0.000 description 34
- 238000010992 reflux Methods 0.000 description 30
- 229920000578 graft copolymer Polymers 0.000 description 26
- 239000000463 material Substances 0.000 description 22
- 239000000470 constituent Substances 0.000 description 17
- 230000002209 hydrophobic effect Effects 0.000 description 16
- 238000000034 method Methods 0.000 description 11
- 238000007792 addition Methods 0.000 description 10
- 230000008569 process Effects 0.000 description 9
- 238000005189 flocculation Methods 0.000 description 8
- 230000016615 flocculation Effects 0.000 description 8
- 239000007787 solid Substances 0.000 description 8
- 230000015572 biosynthetic process Effects 0.000 description 6
- 239000011541 reaction mixture Substances 0.000 description 6
- -1 silica Chemical class 0.000 description 6
- 238000003756 stirring Methods 0.000 description 6
- 238000003786 synthesis reaction Methods 0.000 description 6
- 206010068516 Encapsulation reaction Diseases 0.000 description 5
- CERQOIWHTDAKMF-UHFFFAOYSA-N Methacrylic acid Chemical compound CC(=C)C(O)=O CERQOIWHTDAKMF-UHFFFAOYSA-N 0.000 description 5
- 239000000047 product Substances 0.000 description 5
- VVQNEPGJFQJSBK-UHFFFAOYSA-N Methyl methacrylate Chemical compound COC(=O)C(C)=C VVQNEPGJFQJSBK-UHFFFAOYSA-N 0.000 description 4
- 239000003795 chemical substances by application Substances 0.000 description 4
- 125000005442 diisocyanate group Chemical group 0.000 description 4
- 238000009472 formulation Methods 0.000 description 4
- 238000007641 inkjet printing Methods 0.000 description 4
- 239000004094 surface-active agent Substances 0.000 description 4
- OMIGHNLMNHATMP-UHFFFAOYSA-N 2-hydroxyethyl prop-2-enoate Chemical compound OCCOC(=O)C=C OMIGHNLMNHATMP-UHFFFAOYSA-N 0.000 description 3
- QTBSBXVTEAMEQO-UHFFFAOYSA-N Acetic acid Chemical compound CC(O)=O QTBSBXVTEAMEQO-UHFFFAOYSA-N 0.000 description 3
- 206010063659 Aversion Diseases 0.000 description 3
- WOBHKFSMXKNTIM-UHFFFAOYSA-N Hydroxyethyl methacrylate Chemical compound CC(=C)C(=O)OCCO WOBHKFSMXKNTIM-UHFFFAOYSA-N 0.000 description 3
- SJRJJKPEHAURKC-UHFFFAOYSA-N N-Methylmorpholine Chemical compound CN1CCOCC1 SJRJJKPEHAURKC-UHFFFAOYSA-N 0.000 description 3
- MUBZPKHOEPUJKR-UHFFFAOYSA-N Oxalic acid Chemical compound OC(=O)C(O)=O MUBZPKHOEPUJKR-UHFFFAOYSA-N 0.000 description 3
- KWYUFKZDYYNOTN-UHFFFAOYSA-M Potassium hydroxide Chemical compound [OH-].[K+] KWYUFKZDYYNOTN-UHFFFAOYSA-M 0.000 description 3
- 239000000654 additive Substances 0.000 description 3
- 125000000217 alkyl group Chemical group 0.000 description 3
- 125000003118 aryl group Chemical group 0.000 description 3
- 229920001400 block copolymer Polymers 0.000 description 3
- 125000004432 carbon atom Chemical group C* 0.000 description 3
- KRKNYBCHXYNGOX-UHFFFAOYSA-N citric acid Chemical compound OC(=O)CC(O)(C(O)=O)CC(O)=O KRKNYBCHXYNGOX-UHFFFAOYSA-N 0.000 description 3
- 239000008367 deionised water Substances 0.000 description 3
- 229910021641 deionized water Inorganic materials 0.000 description 3
- MTHSVFCYNBDYFN-UHFFFAOYSA-N diethylene glycol Chemical compound OCCOCCO MTHSVFCYNBDYFN-UHFFFAOYSA-N 0.000 description 3
- 125000000524 functional group Chemical group 0.000 description 3
- 239000004615 ingredient Substances 0.000 description 3
- 239000011159 matrix material Substances 0.000 description 3
- 229910052751 metal Inorganic materials 0.000 description 3
- 239000002184 metal Substances 0.000 description 3
- 230000003472 neutralizing effect Effects 0.000 description 3
- 239000002562 thickening agent Substances 0.000 description 3
- 229920002818 (Hydroxyethyl)methacrylate Polymers 0.000 description 2
- AZYRZNIYJDKRHO-UHFFFAOYSA-N 1,3-bis(2-isocyanatopropan-2-yl)benzene Chemical compound O=C=NC(C)(C)C1=CC=CC(C(C)(C)N=C=O)=C1 AZYRZNIYJDKRHO-UHFFFAOYSA-N 0.000 description 2
- JKNCOURZONDCGV-UHFFFAOYSA-N 2-(dimethylamino)ethyl 2-methylprop-2-enoate Chemical compound CN(C)CCOC(=O)C(C)=C JKNCOURZONDCGV-UHFFFAOYSA-N 0.000 description 2
- GOXQRTZXKQZDDN-UHFFFAOYSA-N 2-Ethylhexyl acrylate Chemical compound CCCCC(CC)COC(=O)C=C GOXQRTZXKQZDDN-UHFFFAOYSA-N 0.000 description 2
- POAOYUHQDCAZBD-UHFFFAOYSA-N 2-butoxyethanol Chemical compound CCCCOCCO POAOYUHQDCAZBD-UHFFFAOYSA-N 0.000 description 2
- WDQMWEYDKDCEHT-UHFFFAOYSA-N 2-ethylhexyl 2-methylprop-2-enoate Chemical compound CCCCC(CC)COC(=O)C(C)=C WDQMWEYDKDCEHT-UHFFFAOYSA-N 0.000 description 2
- AGBXYHCHUYARJY-UHFFFAOYSA-N 2-phenylethenesulfonic acid Chemical compound OS(=O)(=O)C=CC1=CC=CC=C1 AGBXYHCHUYARJY-UHFFFAOYSA-N 0.000 description 2
- IJGRMHOSHXDMSA-UHFFFAOYSA-N Atomic nitrogen Chemical compound N#N IJGRMHOSHXDMSA-UHFFFAOYSA-N 0.000 description 2
- KAKZBPTYRLMSJV-UHFFFAOYSA-N Butadiene Chemical compound C=CC=C KAKZBPTYRLMSJV-UHFFFAOYSA-N 0.000 description 2
- VEXZGXHMUGYJMC-UHFFFAOYSA-N Hydrochloric acid Chemical compound Cl VEXZGXHMUGYJMC-UHFFFAOYSA-N 0.000 description 2
- XEEYBQQBJWHFJM-UHFFFAOYSA-N Iron Chemical compound [Fe] XEEYBQQBJWHFJM-UHFFFAOYSA-N 0.000 description 2
- 239000005058 Isophorone diisocyanate Substances 0.000 description 2
- RRHGJUQNOFWUDK-UHFFFAOYSA-N Isoprene Chemical compound CC(=C)C=C RRHGJUQNOFWUDK-UHFFFAOYSA-N 0.000 description 2
- CERQOIWHTDAKMF-UHFFFAOYSA-M Methacrylate Chemical compound CC(=C)C([O-])=O CERQOIWHTDAKMF-UHFFFAOYSA-M 0.000 description 2
- YNAVUWVOSKDBBP-UHFFFAOYSA-N Morpholine Chemical compound C1COCCN1 YNAVUWVOSKDBBP-UHFFFAOYSA-N 0.000 description 2
- UEEJHVSXFDXPFK-UHFFFAOYSA-N N-dimethylaminoethanol Chemical compound CN(C)CCO UEEJHVSXFDXPFK-UHFFFAOYSA-N 0.000 description 2
- GRYLNZFGIOXLOG-UHFFFAOYSA-N Nitric acid Chemical compound O[N+]([O-])=O GRYLNZFGIOXLOG-UHFFFAOYSA-N 0.000 description 2
- NBIIXXVUZAFLBC-UHFFFAOYSA-N Phosphoric acid Chemical compound OP(O)(O)=O NBIIXXVUZAFLBC-UHFFFAOYSA-N 0.000 description 2
- JUJWROOIHBZHMG-UHFFFAOYSA-N Pyridine Chemical compound C1=CC=NC=C1 JUJWROOIHBZHMG-UHFFFAOYSA-N 0.000 description 2
- VYPSYNLAJGMNEJ-UHFFFAOYSA-N Silicium dioxide Chemical compound O=[Si]=O VYPSYNLAJGMNEJ-UHFFFAOYSA-N 0.000 description 2
- PPBRXRYQALVLMV-UHFFFAOYSA-N Styrene Chemical compound C=CC1=CC=CC=C1 PPBRXRYQALVLMV-UHFFFAOYSA-N 0.000 description 2
- QAOWNCQODCNURD-UHFFFAOYSA-N Sulfuric acid Chemical compound OS(O)(=O)=O QAOWNCQODCNURD-UHFFFAOYSA-N 0.000 description 2
- GWEVSGVZZGPLCZ-UHFFFAOYSA-N Titan oxide Chemical compound O=[Ti]=O GWEVSGVZZGPLCZ-UHFFFAOYSA-N 0.000 description 2
- 230000002411 adverse Effects 0.000 description 2
- 125000000129 anionic group Chemical group 0.000 description 2
- 239000003139 biocide Substances 0.000 description 2
- CQEYYJKEWSMYFG-UHFFFAOYSA-N butyl acrylate Chemical compound CCCCOC(=O)C=C CQEYYJKEWSMYFG-UHFFFAOYSA-N 0.000 description 2
- QXJJQWWVWRCVQT-UHFFFAOYSA-K calcium;sodium;phosphate Chemical compound [Na+].[Ca+2].[O-]P([O-])([O-])=O QXJJQWWVWRCVQT-UHFFFAOYSA-K 0.000 description 2
- 239000003153 chemical reaction reagent Substances 0.000 description 2
- 238000004040 coloring Methods 0.000 description 2
- 239000002537 cosmetic Substances 0.000 description 2
- 229960002887 deanol Drugs 0.000 description 2
- 239000012972 dimethylethanolamine Substances 0.000 description 2
- 239000010408 film Substances 0.000 description 2
- VOZRXNHHFUQHIL-UHFFFAOYSA-N glycidyl methacrylate Chemical group CC(=C)C(=O)OCC1CO1 VOZRXNHHFUQHIL-UHFFFAOYSA-N 0.000 description 2
- RRAMGCGOFNQTLD-UHFFFAOYSA-N hexamethylene diisocyanate Chemical compound O=C=NCCCCCCN=C=O RRAMGCGOFNQTLD-UHFFFAOYSA-N 0.000 description 2
- NIMLQBUJDJZYEJ-UHFFFAOYSA-N isophorone diisocyanate Chemical compound CC1(C)CC(N=C=O)CC(C)(CN=C=O)C1 NIMLQBUJDJZYEJ-UHFFFAOYSA-N 0.000 description 2
- WMFOQBRAJBCJND-UHFFFAOYSA-M lithium hydroxide Inorganic materials [Li+].[OH-] WMFOQBRAJBCJND-UHFFFAOYSA-M 0.000 description 2
- 238000004519 manufacturing process Methods 0.000 description 2
- 150000002734 metacrylic acid derivatives Chemical class 0.000 description 2
- 229910044991 metal oxide Inorganic materials 0.000 description 2
- 150000004706 metal oxides Chemical class 0.000 description 2
- BDAGIHXWWSANSR-UHFFFAOYSA-N methanoic acid Natural products OC=O BDAGIHXWWSANSR-UHFFFAOYSA-N 0.000 description 2
- 125000002496 methyl group Chemical group [H]C([H])([H])* 0.000 description 2
- 150000007522 mineralic acids Chemical class 0.000 description 2
- 229910017604 nitric acid Inorganic materials 0.000 description 2
- 239000002687 nonaqueous vehicle Substances 0.000 description 2
- 230000003287 optical effect Effects 0.000 description 2
- 125000006353 oxyethylene group Chemical group 0.000 description 2
- 102220206201 rs1057524801 Human genes 0.000 description 2
- 150000003839 salts Chemical class 0.000 description 2
- HEMHJVSKTPXQMS-UHFFFAOYSA-M sodium hydroxide Inorganic materials [OH-].[Na+] HEMHJVSKTPXQMS-UHFFFAOYSA-M 0.000 description 2
- 238000003860 storage Methods 0.000 description 2
- 239000000758 substrate Substances 0.000 description 2
- 150000005621 tetraalkylammonium salts Chemical class 0.000 description 2
- WGTYBPLFGIVFAS-UHFFFAOYSA-M tetramethylammonium hydroxide Chemical compound [OH-].C[N+](C)(C)C WGTYBPLFGIVFAS-UHFFFAOYSA-M 0.000 description 2
- 238000005382 thermal cycling Methods 0.000 description 2
- JOXIMZWYDAKGHI-UHFFFAOYSA-N toluene-4-sulfonic acid Chemical compound CC1=CC=C(S(O)(=O)=O)C=C1 JOXIMZWYDAKGHI-UHFFFAOYSA-N 0.000 description 2
- 238000012546 transfer Methods 0.000 description 2
- 239000013638 trimer Substances 0.000 description 2
- GETQZCLCWQTVFV-UHFFFAOYSA-N trimethylamine Chemical compound CN(C)C GETQZCLCWQTVFV-UHFFFAOYSA-N 0.000 description 2
- DTGKSKDOIYIVQL-WEDXCCLWSA-N (+)-borneol Chemical group C1C[C@@]2(C)[C@@H](O)C[C@@H]1C2(C)C DTGKSKDOIYIVQL-WEDXCCLWSA-N 0.000 description 1
- 229940015975 1,2-hexanediol Drugs 0.000 description 1
- PTBDIHRZYDMNKB-UHFFFAOYSA-N 2,2-Bis(hydroxymethyl)propionic acid Chemical compound OCC(C)(CO)C(O)=O PTBDIHRZYDMNKB-UHFFFAOYSA-N 0.000 description 1
- SMZOUWXMTYCWNB-UHFFFAOYSA-N 2-(2-methoxy-5-methylphenyl)ethanamine Chemical compound COC1=CC=C(C)C=C1CCN SMZOUWXMTYCWNB-UHFFFAOYSA-N 0.000 description 1
- JAHNSTQSQJOJLO-UHFFFAOYSA-N 2-(3-fluorophenyl)-1h-imidazole Chemical compound FC1=CC=CC(C=2NC=CN=2)=C1 JAHNSTQSQJOJLO-UHFFFAOYSA-N 0.000 description 1
- SJIXRGNQPBQWMK-UHFFFAOYSA-N 2-(diethylamino)ethyl 2-methylprop-2-enoate Chemical compound CCN(CC)CCOC(=O)C(C)=C SJIXRGNQPBQWMK-UHFFFAOYSA-N 0.000 description 1
- QHVBLSNVXDSMEB-UHFFFAOYSA-N 2-(diethylamino)ethyl prop-2-enoate Chemical compound CCN(CC)CCOC(=O)C=C QHVBLSNVXDSMEB-UHFFFAOYSA-N 0.000 description 1
- DPBJAVGHACCNRL-UHFFFAOYSA-N 2-(dimethylamino)ethyl prop-2-enoate Chemical compound CN(C)CCOC(=O)C=C DPBJAVGHACCNRL-UHFFFAOYSA-N 0.000 description 1
- MXZROAOUCUVNHX-UHFFFAOYSA-N 2-Aminopropanol Chemical compound CCC(N)O MXZROAOUCUVNHX-UHFFFAOYSA-N 0.000 description 1
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- VEXZGXHMUGYJMC-UHFFFAOYSA-M Chloride anion Chemical compound [Cl-] VEXZGXHMUGYJMC-UHFFFAOYSA-M 0.000 description 1
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- 125000003277 amino group Chemical group 0.000 description 1
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- GCTPMLUUWLLESL-UHFFFAOYSA-N benzyl prop-2-enoate Chemical class C=CC(=O)OCC1=CC=CC=C1 GCTPMLUUWLLESL-UHFFFAOYSA-N 0.000 description 1
- 239000011230 binding agent Substances 0.000 description 1
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- 125000000484 butyl group Chemical group [H]C([*])([H])C([H])([H])C([H])([H])C([H])([H])[H] 0.000 description 1
- 125000002091 cationic group Chemical group 0.000 description 1
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- NEHMKBQYUWJMIP-NJFSPNSNSA-N chloro(114C)methane Chemical compound [14CH3]Cl NEHMKBQYUWJMIP-NJFSPNSNSA-N 0.000 description 1
- 238000002508 contact lithography Methods 0.000 description 1
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- 229910052802 copper Inorganic materials 0.000 description 1
- 239000010949 copper Substances 0.000 description 1
- XCJYREBRNVKWGJ-UHFFFAOYSA-N copper(II) phthalocyanine Chemical compound [Cu+2].C12=CC=CC=C2C(N=C2[N-]C(C3=CC=CC=C32)=N2)=NC1=NC([C]1C=CC=CC1=1)=NC=1N=C1[C]3C=CC=CC3=C2[N-]1 XCJYREBRNVKWGJ-UHFFFAOYSA-N 0.000 description 1
- 229920006037 cross link polymer Polymers 0.000 description 1
- 230000002939 deleterious effect Effects 0.000 description 1
- 238000011161 development Methods 0.000 description 1
- 125000004386 diacrylate group Chemical group 0.000 description 1
- 150000004985 diamines Chemical class 0.000 description 1
- 239000012973 diazabicyclooctane Substances 0.000 description 1
- VAYGXNSJCAHWJZ-UHFFFAOYSA-N dimethyl sulfate Chemical compound COS(=O)(=O)OC VAYGXNSJCAHWJZ-UHFFFAOYSA-N 0.000 description 1
- 235000019329 dioctyl sodium sulphosuccinate Nutrition 0.000 description 1
- YHAIUSTWZPMYGG-UHFFFAOYSA-L disodium;2,2-dioctyl-3-sulfobutanedioate Chemical compound [Na+].[Na+].CCCCCCCCC(C([O-])=O)(C(C([O-])=O)S(O)(=O)=O)CCCCCCCC YHAIUSTWZPMYGG-UHFFFAOYSA-L 0.000 description 1
- 125000003438 dodecyl group Chemical group [H]C([H])([H])C([H])([H])C([H])([H])C([H])([H])C([H])([H])C([H])([H])C([H])([H])C([H])([H])C([H])([H])C([H])([H])C([H])([H])C([H])([H])* 0.000 description 1
- 239000000975 dye Substances 0.000 description 1
- 230000000694 effects Effects 0.000 description 1
- 238000005516 engineering process Methods 0.000 description 1
- 230000007613 environmental effect Effects 0.000 description 1
- 125000001495 ethyl group Chemical group [H]C([H])([H])C([H])([H])* 0.000 description 1
- 239000004744 fabric Substances 0.000 description 1
- 239000000835 fiber Substances 0.000 description 1
- 239000010419 fine particle Substances 0.000 description 1
- 238000010304 firing Methods 0.000 description 1
- 230000003311 flocculating effect Effects 0.000 description 1
- 235000019253 formic acid Nutrition 0.000 description 1
- 150000002314 glycerols Chemical class 0.000 description 1
- 229910052736 halogen Inorganic materials 0.000 description 1
- 150000002367 halogens Chemical class 0.000 description 1
- 230000036541 health Effects 0.000 description 1
- 229910001385 heavy metal Inorganic materials 0.000 description 1
- FHKSXSQHXQEMOK-UHFFFAOYSA-N hexane-1,2-diol Chemical compound CCCCC(O)CO FHKSXSQHXQEMOK-UHFFFAOYSA-N 0.000 description 1
- 239000003906 humectant Substances 0.000 description 1
- 239000012535 impurity Substances 0.000 description 1
- 239000002917 insecticide Substances 0.000 description 1
- 230000003993 interaction Effects 0.000 description 1
- 229910052742 iron Inorganic materials 0.000 description 1
- 125000000959 isobutyl group Chemical group [H]C([H])([H])C([H])(C([H])([H])[H])C([H])([H])* 0.000 description 1
- 239000004816 latex Substances 0.000 description 1
- 229920000126 latex Polymers 0.000 description 1
- 229920005684 linear copolymer Polymers 0.000 description 1
- VZCYOOQTPOCHFL-UPHRSURJSA-N maleic acid Chemical compound OC(=O)\C=C/C(O)=O VZCYOOQTPOCHFL-UPHRSURJSA-N 0.000 description 1
- 239000011976 maleic acid Substances 0.000 description 1
- 239000013528 metallic particle Substances 0.000 description 1
- 150000002739 metals Chemical class 0.000 description 1
- 125000005395 methacrylic acid group Chemical group 0.000 description 1
- CRVGTESFCCXCTH-UHFFFAOYSA-N methyl diethanolamine Chemical compound OCCN(C)CCO CRVGTESFCCXCTH-UHFFFAOYSA-N 0.000 description 1
- LVHBHZANLOWSRM-UHFFFAOYSA-N methylenebutanedioic acid Natural products OC(=O)CC(=C)C(O)=O LVHBHZANLOWSRM-UHFFFAOYSA-N 0.000 description 1
- 244000005700 microbiome Species 0.000 description 1
- 229910052757 nitrogen Inorganic materials 0.000 description 1
- 125000001400 nonyl group Chemical group [H]C([*])([H])C([H])([H])C([H])([H])C([H])([H])C([H])([H])C([H])([H])C([H])([H])C([H])([H])C([H])([H])[H] 0.000 description 1
- 150000007524 organic acids Chemical class 0.000 description 1
- 235000006408 oxalic acid Nutrition 0.000 description 1
- 150000002924 oxiranes Chemical group 0.000 description 1
- 230000035515 penetration Effects 0.000 description 1
- 239000000825 pharmaceutical preparation Substances 0.000 description 1
- 230000000704 physical effect Effects 0.000 description 1
- 239000004033 plastic Substances 0.000 description 1
- 229920003023 plastic Polymers 0.000 description 1
- 229920001223 polyethylene glycol Polymers 0.000 description 1
- 238000006116 polymerization reaction Methods 0.000 description 1
- 239000002244 precipitate Substances 0.000 description 1
- 238000002360 preparation method Methods 0.000 description 1
- HJWLCRVIBGQPNF-UHFFFAOYSA-N prop-2-enylbenzene Chemical compound C=CCC1=CC=CC=C1 HJWLCRVIBGQPNF-UHFFFAOYSA-N 0.000 description 1
- 125000001436 propyl group Chemical group [H]C([*])([H])C([H])([H])C([H])([H])[H] 0.000 description 1
- UMJSCPRVCHMLSP-UHFFFAOYSA-N pyridine Natural products COC1=CC=CN=C1 UMJSCPRVCHMLSP-UHFFFAOYSA-N 0.000 description 1
- HNJBEVLQSNELDL-UHFFFAOYSA-N pyrrolidin-2-one Chemical compound O=C1CCCN1 HNJBEVLQSNELDL-UHFFFAOYSA-N 0.000 description 1
- 238000005956 quaternization reaction Methods 0.000 description 1
- 229920005604 random copolymer Polymers 0.000 description 1
- 238000011160 research Methods 0.000 description 1
- 229920005989 resin Polymers 0.000 description 1
- 239000011347 resin Substances 0.000 description 1
- 239000003352 sequestering agent Substances 0.000 description 1
- 239000000377 silicon dioxide Substances 0.000 description 1
- 239000002904 solvent Substances 0.000 description 1
- 239000010959 steel Substances 0.000 description 1
- 150000005846 sugar alcohols Polymers 0.000 description 1
- 239000006228 supernatant Substances 0.000 description 1
- 238000012360 testing method Methods 0.000 description 1
- 229940073455 tetraethylammonium hydroxide Drugs 0.000 description 1
- LRGJRHZIDJQFCL-UHFFFAOYSA-M tetraethylazanium;hydroxide Chemical compound [OH-].CC[N+](CC)(CC)CC LRGJRHZIDJQFCL-UHFFFAOYSA-M 0.000 description 1
- VZCYOOQTPOCHFL-UHFFFAOYSA-N trans-butenedioic acid Natural products OC(=O)C=CC(O)=O VZCYOOQTPOCHFL-UHFFFAOYSA-N 0.000 description 1
- IMNIMPAHZVJRPE-UHFFFAOYSA-N triethylenediamine Chemical compound C1CN2CCN1CC2 IMNIMPAHZVJRPE-UHFFFAOYSA-N 0.000 description 1
- 229960004418 trolamine Drugs 0.000 description 1
- 229920002554 vinyl polymer Polymers 0.000 description 1
- 239000004034 viscosity adjusting agent Substances 0.000 description 1
Classifications
-
- C—CHEMISTRY; METALLURGY
- C09—DYES; PAINTS; POLISHES; NATURAL RESINS; ADHESIVES; COMPOSITIONS NOT OTHERWISE PROVIDED FOR; APPLICATIONS OF MATERIALS NOT OTHERWISE PROVIDED FOR
- C09D—COATING COMPOSITIONS, e.g. PAINTS, VARNISHES OR LACQUERS; FILLING PASTES; CHEMICAL PAINT OR INK REMOVERS; INKS; CORRECTING FLUIDS; WOODSTAINS; PASTES OR SOLIDS FOR COLOURING OR PRINTING; USE OF MATERIALS THEREFOR
- C09D11/00—Inks
- C09D11/30—Inkjet printing inks
- C09D11/32—Inkjet printing inks characterised by colouring agents
- C09D11/324—Inkjet printing inks characterised by colouring agents containing carbon black
- C09D11/326—Inkjet printing inks characterised by colouring agents containing carbon black characterised by the pigment dispersant
-
- C—CHEMISTRY; METALLURGY
- C09—DYES; PAINTS; POLISHES; NATURAL RESINS; ADHESIVES; COMPOSITIONS NOT OTHERWISE PROVIDED FOR; APPLICATIONS OF MATERIALS NOT OTHERWISE PROVIDED FOR
- C09D—COATING COMPOSITIONS, e.g. PAINTS, VARNISHES OR LACQUERS; FILLING PASTES; CHEMICAL PAINT OR INK REMOVERS; INKS; CORRECTING FLUIDS; WOODSTAINS; PASTES OR SOLIDS FOR COLOURING OR PRINTING; USE OF MATERIALS THEREFOR
- C09D5/00—Coating compositions, e.g. paints, varnishes or lacquers, characterised by their physical nature or the effects produced; Filling pastes
- C09D5/02—Emulsion paints including aerosols
-
- B—PERFORMING OPERATIONS; TRANSPORTING
- B01—PHYSICAL OR CHEMICAL PROCESSES OR APPARATUS IN GENERAL
- B01J—CHEMICAL OR PHYSICAL PROCESSES, e.g. CATALYSIS OR COLLOID CHEMISTRY; THEIR RELEVANT APPARATUS
- B01J13/00—Colloid chemistry, e.g. the production of colloidal materials or their solutions, not otherwise provided for; Making microcapsules or microballoons
- B01J13/0004—Preparation of sols
- B01J13/0034—Additives, e.g. in view of promoting stabilisation or peptisation
-
- B—PERFORMING OPERATIONS; TRANSPORTING
- B01—PHYSICAL OR CHEMICAL PROCESSES OR APPARATUS IN GENERAL
- B01J—CHEMICAL OR PHYSICAL PROCESSES, e.g. CATALYSIS OR COLLOID CHEMISTRY; THEIR RELEVANT APPARATUS
- B01J13/00—Colloid chemistry, e.g. the production of colloidal materials or their solutions, not otherwise provided for; Making microcapsules or microballoons
- B01J13/0004—Preparation of sols
- B01J13/0039—Post treatment
-
- B—PERFORMING OPERATIONS; TRANSPORTING
- B01—PHYSICAL OR CHEMICAL PROCESSES OR APPARATUS IN GENERAL
- B01J—CHEMICAL OR PHYSICAL PROCESSES, e.g. CATALYSIS OR COLLOID CHEMISTRY; THEIR RELEVANT APPARATUS
- B01J13/00—Colloid chemistry, e.g. the production of colloidal materials or their solutions, not otherwise provided for; Making microcapsules or microballoons
- B01J13/0086—Preparation of sols by physical processes
-
- B—PERFORMING OPERATIONS; TRANSPORTING
- B01—PHYSICAL OR CHEMICAL PROCESSES OR APPARATUS IN GENERAL
- B01J—CHEMICAL OR PHYSICAL PROCESSES, e.g. CATALYSIS OR COLLOID CHEMISTRY; THEIR RELEVANT APPARATUS
- B01J13/00—Colloid chemistry, e.g. the production of colloidal materials or their solutions, not otherwise provided for; Making microcapsules or microballoons
- B01J13/02—Making microcapsules or microballoons
- B01J13/06—Making microcapsules or microballoons by phase separation
- B01J13/14—Polymerisation; cross-linking
- B01J13/16—Interfacial polymerisation
-
- C—CHEMISTRY; METALLURGY
- C08—ORGANIC MACROMOLECULAR COMPOUNDS; THEIR PREPARATION OR CHEMICAL WORKING-UP; COMPOSITIONS BASED THEREON
- C08G—MACROMOLECULAR COMPOUNDS OBTAINED OTHERWISE THAN BY REACTIONS ONLY INVOLVING UNSATURATED CARBON-TO-CARBON BONDS
- C08G18/00—Polymeric products of isocyanates or isothiocyanates
- C08G18/06—Polymeric products of isocyanates or isothiocyanates with compounds having active hydrogen
- C08G18/28—Polymeric products of isocyanates or isothiocyanates with compounds having active hydrogen characterised by the compounds used containing active hydrogen
- C08G18/40—High-molecular-weight compounds
- C08G18/62—Polymers of compounds having carbon-to-carbon double bonds
- C08G18/6216—Polymers of alpha-beta ethylenically unsaturated carboxylic acids or of derivatives thereof
- C08G18/625—Polymers of alpha-beta ethylenically unsaturated carboxylic acids; hydrolyzed polymers of esters of these acids
- C08G18/6254—Polymers of alpha-beta ethylenically unsaturated carboxylic acids and of esters of these acids containing hydroxy groups
-
- C—CHEMISTRY; METALLURGY
- C08—ORGANIC MACROMOLECULAR COMPOUNDS; THEIR PREPARATION OR CHEMICAL WORKING-UP; COMPOSITIONS BASED THEREON
- C08G—MACROMOLECULAR COMPOUNDS OBTAINED OTHERWISE THAN BY REACTIONS ONLY INVOLVING UNSATURATED CARBON-TO-CARBON BONDS
- C08G18/00—Polymeric products of isocyanates or isothiocyanates
- C08G18/06—Polymeric products of isocyanates or isothiocyanates with compounds having active hydrogen
- C08G18/28—Polymeric products of isocyanates or isothiocyanates with compounds having active hydrogen characterised by the compounds used containing active hydrogen
- C08G18/40—High-molecular-weight compounds
- C08G18/62—Polymers of compounds having carbon-to-carbon double bonds
- C08G18/6283—Polymers of nitrogen containing compounds having carbon-to-carbon double bonds
-
- C—CHEMISTRY; METALLURGY
- C09—DYES; PAINTS; POLISHES; NATURAL RESINS; ADHESIVES; COMPOSITIONS NOT OTHERWISE PROVIDED FOR; APPLICATIONS OF MATERIALS NOT OTHERWISE PROVIDED FOR
- C09B—ORGANIC DYES OR CLOSELY-RELATED COMPOUNDS FOR PRODUCING DYES, e.g. PIGMENTS; MORDANTS; LAKES
- C09B67/00—Influencing the physical, e.g. the dyeing or printing properties of dyestuffs without chemical reactions, e.g. by treating with solvents grinding or grinding assistants, coating of pigments or dyes; Process features in the making of dyestuff preparations; Dyestuff preparations of a special physical nature, e.g. tablets, films
- C09B67/0001—Post-treatment of organic pigments or dyes
- C09B67/0004—Coated particulate pigments or dyes
- C09B67/0008—Coated particulate pigments or dyes with organic coatings
- C09B67/0013—Coated particulate pigments or dyes with organic coatings with polymeric coatings
-
- C—CHEMISTRY; METALLURGY
- C09—DYES; PAINTS; POLISHES; NATURAL RESINS; ADHESIVES; COMPOSITIONS NOT OTHERWISE PROVIDED FOR; APPLICATIONS OF MATERIALS NOT OTHERWISE PROVIDED FOR
- C09B—ORGANIC DYES OR CLOSELY-RELATED COMPOUNDS FOR PRODUCING DYES, e.g. PIGMENTS; MORDANTS; LAKES
- C09B67/00—Influencing the physical, e.g. the dyeing or printing properties of dyestuffs without chemical reactions, e.g. by treating with solvents grinding or grinding assistants, coating of pigments or dyes; Process features in the making of dyestuff preparations; Dyestuff preparations of a special physical nature, e.g. tablets, films
- C09B67/0071—Process features in the making of dyestuff preparations; Dehydrating agents; Dispersing agents; Dustfree compositions
- C09B67/0084—Dispersions of dyes
-
- C—CHEMISTRY; METALLURGY
- C09—DYES; PAINTS; POLISHES; NATURAL RESINS; ADHESIVES; COMPOSITIONS NOT OTHERWISE PROVIDED FOR; APPLICATIONS OF MATERIALS NOT OTHERWISE PROVIDED FOR
- C09B—ORGANIC DYES OR CLOSELY-RELATED COMPOUNDS FOR PRODUCING DYES, e.g. PIGMENTS; MORDANTS; LAKES
- C09B67/00—Influencing the physical, e.g. the dyeing or printing properties of dyestuffs without chemical reactions, e.g. by treating with solvents grinding or grinding assistants, coating of pigments or dyes; Process features in the making of dyestuff preparations; Dyestuff preparations of a special physical nature, e.g. tablets, films
- C09B67/0071—Process features in the making of dyestuff preparations; Dehydrating agents; Dispersing agents; Dustfree compositions
- C09B67/0084—Dispersions of dyes
- C09B67/0085—Non common dispersing agents
- C09B67/009—Non common dispersing agents polymeric dispersing agent
-
- C—CHEMISTRY; METALLURGY
- C09—DYES; PAINTS; POLISHES; NATURAL RESINS; ADHESIVES; COMPOSITIONS NOT OTHERWISE PROVIDED FOR; APPLICATIONS OF MATERIALS NOT OTHERWISE PROVIDED FOR
- C09D—COATING COMPOSITIONS, e.g. PAINTS, VARNISHES OR LACQUERS; FILLING PASTES; CHEMICAL PAINT OR INK REMOVERS; INKS; CORRECTING FLUIDS; WOODSTAINS; PASTES OR SOLIDS FOR COLOURING OR PRINTING; USE OF MATERIALS THEREFOR
- C09D17/00—Pigment pastes, e.g. for mixing in paints
-
- C—CHEMISTRY; METALLURGY
- C09—DYES; PAINTS; POLISHES; NATURAL RESINS; ADHESIVES; COMPOSITIONS NOT OTHERWISE PROVIDED FOR; APPLICATIONS OF MATERIALS NOT OTHERWISE PROVIDED FOR
- C09D—COATING COMPOSITIONS, e.g. PAINTS, VARNISHES OR LACQUERS; FILLING PASTES; CHEMICAL PAINT OR INK REMOVERS; INKS; CORRECTING FLUIDS; WOODSTAINS; PASTES OR SOLIDS FOR COLOURING OR PRINTING; USE OF MATERIALS THEREFOR
- C09D5/00—Coating compositions, e.g. paints, varnishes or lacquers, characterised by their physical nature or the effects produced; Filling pastes
- C09D5/02—Emulsion paints including aerosols
- C09D5/024—Emulsion paints including aerosols characterised by the additives
- C09D5/027—Dispersing agents
-
- C—CHEMISTRY; METALLURGY
- C09—DYES; PAINTS; POLISHES; NATURAL RESINS; ADHESIVES; COMPOSITIONS NOT OTHERWISE PROVIDED FOR; APPLICATIONS OF MATERIALS NOT OTHERWISE PROVIDED FOR
- C09K—MATERIALS FOR MISCELLANEOUS APPLICATIONS, NOT PROVIDED FOR ELSEWHERE
- C09K23/00—Use of substances as emulsifying, wetting, dispersing, or foam-producing agents
- C09K23/16—Amines or polyamines
-
- C—CHEMISTRY; METALLURGY
- C09—DYES; PAINTS; POLISHES; NATURAL RESINS; ADHESIVES; COMPOSITIONS NOT OTHERWISE PROVIDED FOR; APPLICATIONS OF MATERIALS NOT OTHERWISE PROVIDED FOR
- C09K—MATERIALS FOR MISCELLANEOUS APPLICATIONS, NOT PROVIDED FOR ELSEWHERE
- C09K23/00—Use of substances as emulsifying, wetting, dispersing, or foam-producing agents
- C09K23/54—Silicon compounds
Definitions
- This invention relates to dispersions of particles in a liquid vehicle and, more particularly, to dispersions in which the particles are entangled in a cross-linked polymer matrix.
- Dispersions of particles in a liquid vehicle are commonly used in a wide variety of industries and processes, such as coatings (e.g., paint and ink), magnetic or optical recording media (e.g., tapes and disks), cosmetics (e.g., lipsticks and nail polish); agriculture (e.g., insecticides), pharmaceutical preparations and many others.
- coatings e.g., paint and ink
- magnetic or optical recording media e.g., tapes and disks
- cosmetics e.g., lipsticks and nail polish
- agriculture e.g., insecticides
- these dispersions are very diverse. Generally speaking, however, these dispersions all contain a liquid vehicle (such as water, an organic solvent, or a combination of the two) and some type of particle (such as a pigment, a pharmaceutically active compound, metallic flakes, hollow glass spheres, discrete polymer particles, etc.).
- a dispersant is used to help maintain the particles in a suspended state in the liquid vehicle; i.e., prevent the particles from settling out of the liquid.
- the dispersant used is a polymer.
- Inkjet printing is a non-impact and non- contact printing process in which an electronic signal produces droplets of ink that are deposited on a wide variety of substrates such as paper, transparent film, plastics, metals and fabrics.
- the ink is ejected from a printhead containing a plurality of very small nozzles using thermal or piezoelectric ejection technology.
- ink jet printing it is critical that the ink components remain stable, not only in storage but also over repeated firing cycles; that they not interact with the components used to manufacture the printhead; that they not clog the nozzle openings; and that they not for a film on the orifice plate or resistors used in the printhead.
- inks tend to be aqueous based dispersions.
- the present invention provides a dispersion of particles in a liquid vehicle, comprising: (a) a liquid vehicle selected from the group consisting of water, organic solvents and combinations thereof;
- a polymer dispersant having at least one segment soluble in the liquid vehicle and at least one segment insoluble in the liquid vehicle, (d) wherein said at least one insoluble segment has cross-linking moieties that are cross-linked to at least one cross-linkable component which is at least substantially insoluble in the liquid medium and is selected from the group consisting of itself, a polyfunctional monomer, a poly functional oligomer, and a polyfunctional polymer to form an encapsulation network which entraps the particles.
- the dispersion may also contain a catalyst to facilitate the cross-linking reaction.
- the particles may be organic or inorganic and the particles may or may not be covalently bonded to the dispersant.
- Figure 1 is a schematic illustration of the natural orientation of a graft copolymer having soluble and insoluble segments and an insoluble particle in a liquid medium.
- Figure 2 is a schematic illustration of an entrapped particle in the dispersions of the present invention, particularly illustrating the cross-linked insoluble segment of the polymer (in this instance a graft copolymer).
- the dispersions of this invention essentially comprise a liquid vehicle, particles and a dispersant polymer that has been cross-linked to entrap the particles.
- the dispersion may contain a cross-linking component and catalysts.
- various additives and adjuvants may be used in the dispersion as is common in the particular application of interest.
- the liquid vehicle while an essential component of the invention, may be aqueous or non-aqueous and may contain water, organic solvents or combinations thereof.
- the particular type and amount of liquid will be readily determined by the particular end use of the dispersions.
- the paint industry utilizes both solvent based and aqueous based paints, stains and coatings.
- the vehicle In ink jet ink applications, the vehicle typically comprises a mixture of water and at least one water soluble organic solvent, most commonly a pyrrolidone or a polyhydric alcohol, or both.
- an aqueous based liquid vehicle i.e., a liquid vehicle comprising at least 50% by weight of water
- Particles i.e., a liquid vehicle comprising at least 50% by weight of water
- the type and composition of the particles is not particularly critical and will largely depend upon the ultimate end use application of the dispersion.
- the particles are at least substantially insoluble in the liquid vehicle. If they were soluble, the resulting mixture would be a solution rather than a dispersion.
- the particles may be organic, inorganic or mixtures thereof. Examples of suitable particles include pigments, insoluble dyes, metallic particles, biologically active compounds, pharmaceutically active compounds, polymer particles, hollow glass spheres, etc.
- the particle size can have an effect on dispersion stability. In general, smaller particles tend to create more stable dispersions in that Brownian motion helps to prevent the particles from flocculating or settling. Small particle size pigments also produce maximum color strength and there fore may be desirable in applications using pigment dispersions.
- the particle size will vary substantially depending upon the desired end use for the dispersion. For ink jet ink applications, for example, a useful particle size will be in the range of 0.005 to 15 microns. For paints, the particle size may be as high as 75 to 100 microns and in other coatings the particles may be up to several hundred microns. One of ordinary skill in the art can readily determine the appropriate particle size for the desired application.
- Fine particles of metal such as copper, iron, steel, aluminum and alloys
- metal oxides e.g., silica, alumina, titania
- metal and metal oxides are suitable for the preparation of magnetic and/or optical recording media.
- some coating applications might utilize metallic flakes in combination with pigments to provide a "pearl-like" finish.
- the amount of particles used in the dispersion is not critical to the invention and can be as desired for the end use application.
- paints, inks and cosmetics may require significantly greater particle concentrations on a weight basis compared to dispersions of highly reactive pharmaceutical or agricultural compounds.
- the particles comprise pigments.
- the function of the polymeric dispersant is to disperse the insoluble particles in the liquid vehicle.
- Structured polymers are particularly preferred.
- the term "structured polymer” means any polymer that does not have a random structure. Stated differently, the term “structured polymer” means that the polymer has identifiable and defined segments or areas based on the type, identity and/or behavior of the monomers contained within the segment or area. Typically, but not always, those segments are characterized as being hydrophobic or hydrophilic.
- structured polymers include block polymers, graft polymers, tapered polymers and branch polymers.
- Particularly preferred structured polymeric dispersants for use in the present invention are block and graft copolymers. Structured polymers are particularly preferred because it is easier to produce segments having the desired functionality in such polymers versus random polymers. Graft polymers having an insoluble backbone and soluble arms are particularly preferred.
- Such polymers can be prepared by techniques well known in the art. For example, block polymers can be made using the well known Group Transfer Polymerization technique and graft polymers may be prepared using chain transfer agents. Specific conditions for preparing particularly preferred polymers are set forth in the examples.
- the polymer dispersant it must contain one or more segments that are soluble in the liquid vehicle and one or more segments that are insoluble in the vehicle.
- the polymer has an area or segment that has an affinity for the liquid vehicle and an area or segment that has an aversion for the liquid vehicle.
- the polymer When the polymer is placed into the liquid, it will naturally tend to orient itself such that the segment(s) with aversion to the liquid is/are clustered together to form a liquid adverse "core" and the segment(s) with affinity for the vehicle are aligned away from the core.
- the particles, which are insoluble and thus also have an aversion for the liquid tend to migrate into the "core" formed by the polymer alignment.
- Figure 1 where 10 is a particle disposed within a core 12 formed by the natural orientation of the polymer 14 (in this instance an graft copolymer) having a soluble arms 16, 16 and an insoluble backbone 18.
- the insoluble particle is relatively content to stay isolated in this liquid free "core". Under certain conditions, however, such as changes in temperature, changes in composition of the liquid vehicle, etc. the particles tend to move out of the core where they can flocculate and precipitate.
- the present invention addresses this problem by cross-linking the insoluble polymer segment to form a network or matrix around the particle which is extremely resistant to changes in liquid vehicle composition, temperature and other factors known to destabilize dispersions.
- the particle 20 is entrapped in a network formed by the insoluble polymer segment 22 and the cross-linking bonds 24.
- the cross-linking bonds 24 are very stable and effectively prevent the particle from leaving the "core" formed by the polymer.
- the soluble segment of the polymer 26 remains aligned into the liquid vehicle and away from the liquid adverse "core".
- the particle 20 it is not necessary that the particle 20 be covalently bonded to the polymer dispersant to obtain the improved dispersion stability.
- the dispersions of the present invention do not preclude situations where the particle, in addition to being entrapped in the cross-linked matrix, would also be covalently bonded to the polymer.
- the monomer composition of the soluble segment and the insoluble segment of the dispersant will, of course, depend upon the liquid vehicle selected for the dispersion. If an aqueous vehicle is selected, the soluble segment will contain hydrophilic monomers and the insoluble segment will contain hydrophobic monomers.' If a non-aqueous vehicle (that is, one containing primarily organic solvents) is selected, the opposite would be true. Therefore, for ease of reference, the useful monomers can be classified generally as hydrophobic or hydrophilic and will be so categorized herein. It is also possible to introduce solubility by making a salt of the monomers used in the soluble segment, particularly for aqueous dispersions, as is known in the art. Whatever the precise composition of the soluble segment may be, it is important that this segment be such that the entire polymer dispersant (or a salt thereof) is soluble in the liquid vehicle.
- Hydrophobic and hydrophilic monomers are well known to those skilled in the art. Particularly useful hydrophobic monomers (which are soluble in a non-aqueous vehicle) include:
- hydrophilic monomers include: (1) acid monomers such as acrylic acid, methacrylic acid, acrylamidomethylpropane sulfonic acid, itaconic acid, maleic acid and styrene sulfonic acid; (2) amine-containing monomers such as 2-dimethylaminoethyl methacrylate, 2-dimethylaminoethyl acrylate, 2-diethylaminoethyl methacrylate, and 2-diethylaminoethyl acrylate; and (3) monomers having oligoether moieties of the general formula:
- Suitable reagents to neutralize the acid monomers include mono-, di-, tri-methylamine, morpholine, n-methyl morpholine; alcohol amines such as dimethylethanolamine (DMEA), methyldiethanolamine, mono-, di-, and tri-ethanolamine; pyridine; ammonium hydroxide; tetra-alkylammonium salts such as tetramethylammonium hydroxide, tetraethyl- ammonium hydroxide; alkali metals hydroxides such as lithium, sodium and potassium hydroxide, aminopropanol, etc.
- DMEA dimethylethanolamine
- pyridine pyridine
- ammonium hydroxide tetra-alkylammonium salts such as tetramethylammonium hydroxide, tetraethyl- ammonium hydroxide
- alkali metals hydroxides such as lithium, sodium and potassium hydroxide, aminopropanol, etc.
- the amine monomers may be neutralized with inorganic and organic acid such as acetic acid, formic acid, oxalic acid, dimethylol propionic acid, hydrochloric acid, p-toluene sulfonic acid, benzene sulfonic acid, nitric acid, citric acid, and the like; halogens such as chloride, fluoride, and bromide, and inorganic acids, such as sulfuric acid, nitric acid, phosphoric acid and the like.
- inorganic and organic acid such as acetic acid, formic acid, oxalic acid, dimethylol propionic acid, hydrochloric acid, p-toluene sulfonic acid, benzene sulfonic acid, nitric acid, citric acid, and the like
- halogens such as chloride, fluoride, and bromide
- inorganic acids such as sulfuric acid, nitric acid, phosphoric acid
- the amino group into a tetra-alkyl ammonium salt
- the amine functionalities can be rendered water-soluble by quaternization with reagents such as benzyl chloride, dimethylsulfate, methyl chloride, etc.
- the polymer can be slightly or completely water soluble.
- the solubility of the polymer increases as the number of oxyethylene units increases.
- the monomers having oligoether moieties can be advantageously used to adjust the physical properties, such as Tg, of the polymer dispersant.
- the insoluble segment(s) of the polymer have cross-linkable functional moieties.
- the insoluble segment(s) of the dispersant is thus capable of cross-linking to itself or to an additional cross-linking compound (e.g., monomer, oligomer, or polymer) that has suitable cross-linking functionality.
- Table 1 identifies suitable functional groups that may be incorporated into the insoluble segment of the dispersant and the companion cross-linking group that may be present in the cross-linking compound.
- cross-linking combinations are the epoxy moieties with amines, hydroxyl moieties with isocyanates and silane moieties with themselves.
- the functional group and the cross-linking group can be incorporated into the insoluble segment(s) of the polymer dispersant by selection of appropriate monomers or, preferably, a separate cross-linking compound having the appropriate group is added to the dispersion.
- Useful cross-linking compounds are those which are insoluble in the liquid vehicle and which do not have significant reaction with the major component of the liquid vehicle.
- useful cross-linking compounds include diacrylate, diisocyanate, m-tetramethylxylene diisocyanate ("m-TMXDI”), hexamethylene diisocyanate trimer (“HMDI”) and isophorone diisocyanate trimer (“IPDI”).
- m- TMXDI is particularly preferred.
- the dispersions of the present invention are made in essentially the same manner as dispersions in the prior art. The particles are premixed with the selected dispersant and then charged to a suitable dispersion apparatus (e.g., a media mill, attritor, 2-roll mill, etc.) and thoroughly mixed.
- a suitable dispersion apparatus e.g., a media mill, attritor, 2-roll mill, etc.
- the cross-linking reaction then takes place and the cross-linking compound (if used) is added to the mixture.
- a catalysts can be those that are either soluble or insoluble in the liquid and are selected depending upon the cross- linking groups.
- suitable catalysts include (for aqueous systems) dibutyltin dilaurate (“DBTDL”), tributyl amine (“TBA”), trioctyl amine, tridodecyl amine and dimethyldodecyl amine.
- DBTDL and TBA are particularly preferred for aqueous dispersions.
- DABCO 2,2,2-diaminobicyclooctane
- DABCO 2,2,2-diaminobicyclooctane
- the dispersions of this invention may also contain other ingredients or additives depending on the particular end use.
- surfactants are commonly used in coatings such as paint or inks to alter surface tension as well as maximize penetration into the substrate (for ink applications in particular). Normally, care must be taken in selecting the surfactant, however, because the surfactant can compete for the particles (i.e., pigments) and thus may destabilize the dispersion. The entrapment of the particles in accordance with the present invention, however, should permit greater latitude in selecting surfactants.
- Biocides are also commonly used in dispersions to inhibit growth of microorganisms. Sequestering agents, such as EDTA, are also commonly used to eliminate deleterious effects of heavy metal impurities.
- Other common additives include humectants, viscosity modifiers, binders, coating aides, thickeners and the like, depending on the desired end use of the dispersion.
- This Example describes the synthesis, dispersion and encapsulation of a graft copolymer with anionic hydrophilic arms, and a hydrophobic backbone.
- a macromonomer was prepared by charging the following components to a 2 liter flask equipped with a thermocouple, stirrer, dropping funnels, reflux condenser, and the means for bubbling nitrogen through the reaction.
- Portion 1 was heated to its reflux temperature in about 15 minutes. Portion 2 was thoroughly mixed and added all at once and the composition was held at its reflux temperature for 5 minutes. The vessel which contained Portion 2 was rinsed with Portion 3, which was then added to the reaction vessel. Portions 4 and 5 were added simultaneously to the reaction vessel while the vessel maintained its reflux temperature. For Portion 4, the first 54.8% was added over 90 minutes, and the remaining 45.2% was added over 240 minutes. For Portion 5, the first 67% was added over 120 minutes and the remaining 33% was added over an additional 120 minutes. After Portions 4 and 5 have been added to the vessel, the reaction is held at reflux for an additional 45 minutes and then cooled to room temperature. The resulting macromonomer solution has a solids content of approximately 50%, and contained 60% methyl methacrylate and 40% methacrylic acid. This polymer has an approximate weight average molecular weight of 3100, and number average molecular weight of 2000.
- a graft copolymer was then prepared from the macromonomer by charging the following components to a 10 liter flask equipped as above:
- Portion 1 was heated to reflux temperature over a period of approximately
- Portion 2 was mixed and charged to the reactor in two equal portions. After the first was added, the reaction was held at reflux for 10 minutes before the second half was added. After the second half of Portion 2 was added, the reaction was held at reflux for 10 minutes. Portions 3 and 4 were added simultaneously to the reaction vessel while maintaining a reflux in the reaction vessel. Portion 3 was added over 180 minutes, and Portion 4 was added over 240 minutes. After the additions of Portions 3 and 4 were completed, Portion 5 was added to the reaction vessel over 15 minutes, maintaining the reflux temperature. After the addition of Portion 5 was completed, the reaction mixture was maintained at reflux for 120 minutes and then cooled to room temperature.
- the resulting graft copolymer solution had a solids content of approximately 63% by weight and had the following overall approximate composition: 33.25%) 2-ethylhexyl acrylate; 36.75% hydroxyethyl acrylate; 18%) methyl methacrylate and 12% methacrylic acid.
- This material had a weight average molecular weight of approximately 21 ,000 and a number average molecular weight of approximately 7800.
- a waterborne pigment dispersion was prepared by charging the following constituents into an 01 -Attritor media mill:
- the graft copolymer is mixed with the neutralizing agent (AMP) and deionized water to form Portion 1.
- AMP neutralizing agent
- the material from Portion 1 was mixed with the materials in Portion 2 and the constituents were ground for 16 hours at 500 rpm in an 01 -Attritor at 100°F.
- a uniform, transparent, waterborne pigment dispersion was formed that was stable and deflocculated and had a pH range of 7.5-8.5. This dispersion contains 15% pigment and 10% polymer.
- This material was used in an encapsulation reaction that involves a crosslinking reaction between hydroxyl groups in the backbone and a hydrophobic diisocyanate/catalyst system.
- This Example describes the synthesis, dispersion and encapsulation of a graft copolymer with nonionic hydrophilic arms, and a hydrophobic backbone.
- Portion 1 was heated to reflux temperature over a period of approximately 20 minutes. Portions 2 and 3 were added simultaneously to the reaction vessel while maintaining a reflux in the reaction vessel. Portion 2 was added over 180 minutes, and Portion 3 was added over 240 minutes. After the additions of Portions 2 and 3 were completed, Portion 4 was added to the reaction vessel over 15 minutes, maintaining the reflux temperature. After the addition of Portion 4 was completed, the reaction mixture was maintained at reflux for 120 minutes and then cooled to room temperature.
- the resulting graft copolymer solution had a solids content of approximately 40% by weight and had the following overall approximate composition: 19% n-butyl acrylate; 21% > hydroxyethyl acrylate; and 60%) Bisomer S20W. This material had a weight average molecular weight of approximately 12300 and a number average molecular weight of approximately 5700.
- a waterborne pigment dispersion was prepared by charging the following constituents into an 01 -Attritor media mill:
- the graft copolymer is mixed with the deionized water to form Portion 1 (no neutralizing agent is needed).
- the material from Portion 1 was mixed with the materials in Portion 2 and the constituents were ground for 16 hours at 500 ⁇ m in an 01 -Attritor at 100°F.
- a uniform, transparent, waterborne pigment dispersion was formed that was stable and deflocculated and had a pH range of 2-4. This dispersion contains 15% pigment and 10%> polymer.
- This material was used in an encapsulation reaction that involves a crosslinking reaction between hydroxy groups in the backbone and a hydrophobic dissocyanate/catalyst system.
- This Examples describes the synthesis, dispersion and encapsulation of a graft copolymer with cationic hydrophilic arms, and a hydrophobic backbone.
- Portion 1 was heated to reflux temperature over a period of approximately 20 minutes.
- Portion 2 was added to Portion 1 in two equal portions 10 minutes apart. After the second half of Portion 2 has been added, the reaction is held at reflux for 10 minutes.
- Portions 3 and 4 were added simultaneously to the reaction vessel while maintaining a reflux. Portion 3 was added over 180 minutes, and Portion 4 was added over 240 minutes. After the additions of Portions 3 and 4 were completed, Portion 5 was added to the reaction vessel over 15 minutes, maintaining the reflux temperature. After the addition of Portion 5 was completed, the reaction mixture was maintained at reflux for 120 minutes and then cooled to room temperature.
- the resulting graft copolymer solution had a solids content of approximately 65%> by weight and had the following overall approximate composition: 33% 2-ethylhexyl acrylate; 37% hydroxyethyl acrylate; and 30% DMAEMA macromonomer.
- This material had a weight average molecular weight of approximately 7337 and a number average molecular weight of approximately 3252.
- a waterborne pigment dispersion was prepared by charging the following constituents into an 01 -Attritor media mill:
- the graft copolymer is neutralized with the 0. IN HC1 to form Portion 1.
- the material from Portion 1 was mixed with the materials in Portion 2 and the constituents were ground for 16 hours at 500 ⁇ m in an 01 -Attritor at 100°F.
- a uniform, transparent, waterborne pigment dispersion was formed that was stable and deflocculated and had a pH range of 2-4. This dispersion contains 15% pigment and 10%> polymer.
- This material was used in an encapsulation process involving a crosslinking reaction between hydroxyl groups in the backbone and a hydrophobic diisocyanate/catalyst system.
- This Example describes the synthesis, dispersion and encapsulation of a block copolymer with an anionic hydrophilic block, and a hydrophobic block.
- Portion 1 was placed in the reactor and heated to reflux temperature over a period of approximately 20 minutes.
- Portion 2 was added to Portion 1 as a single shot and the reaction was held for 5 minutes.
- Portions 3 and 4 were each mixed thoroughly and added simultaneously to the reaction vessel while maintaining a reflux in the reaction vessel.
- Portion 3 was added over 240 minutes, and Portion 4 was added over 270 minutes. After the additions of Portions 3 and 4 were completed, the reaction mixture was maintained at reflux for at least 30 minutes and then cooled to room temperature.
- the resulting block copolymer solution had a solids content of approximately 60%) by weight and had the following overall approximate composition: 33%> 2-ethylhexyl methacrylate; 36%> hydroxyethyl methacrylate; 18% methyl methacrylate and 12% methacrylic acid.
- a waterborne pigment dispersion was prepared by charging the following constituents into an 01 -Attritor media mill:
- the graft copolymer is neutralized with AMP to form Portion 1.
- the material from Portion 1 was mixed with the materials in Portion 2 and the constituents were ground for 16 hours at 500 ⁇ m in an 01 -Attritor at 100°F.
- a uniform, transparent, waterborne pigment dispersion was formed that was stable and deflocculated and had a pH range of 2-4. This dispersion contains 15%> pigment and 10%) polymer.
- This material was then used in an encapsulation reaction involving a crosslinking reaction between hydroxyl groups in the hydrophobic block and a hydrophobic diisocyanate/catalyst system.
- Example 1 The above constituents mixed together and heated at 40-50°C, with efficient stirring, for a period of 6 hours. After this time period, the mixture is cooled to room temperature and tested for flocculation stability as in Example 1 , with the same results.
- This Example describes the synthesis, dispersion and encapsulation of a random, linear copolymer containing the same portion reactive functional groups and monomers seen in Examples 1 and 4.
- Portion 1 was placed in the reactor and heated to reflux temperature over a period of approximately 20 minutes. Portion 2 was added to Portion 1 over one minute and the reaction was held for 5 minutes. Portions 3 and 4 were added simultaneously to the reaction vessel while maintaining a reflux in the reaction vessel. Portion 3 was added over 240 minutes, and Portion 4 was added over 300 minutes. After the additions of Portions 3 and 4 were completed, the reaction mixture was maintained at reflux for at least 30 minutes and then cooled to room temperature.
- the resulting linear, random copolymer solution had a solids content of approximately 58%> by weight and had the following overall approximate composition: 33%> 2-ethylhexyl methacrylate; 36% hydroxyethyl methacrylate; 18%) methyl methacrylate and 12% methacrylic acid.
- a waterborne pigment dispersion was prepared by charging the following constituents into an 01 -Attritor media mill:
- the copolymer is neutralized with the AMP to form Portion 1.
- the material from Portion 1 was mixed with the materials in Portion 2 and the constituents were ground for 16 hours at 500 ⁇ m in an 01 -Attritor at 100°F.
- a uniform, transparent, waterborne pigment dispersion was formed that was stable and deflocculated and had a pH range of 2-4. This dispersion contains 15% pigment and 10%) polymer.
- This material was used in the following encapsulation reaction.
- Example 1 The above constituents mixed together and heated at 40-50°C, with efficient stirring, for a period of 6 hours. After this time period, the mixture is cooled to room temperature and tested for flocculation stability as in Example 1. The encapsulated samples were more stable.
- This Example describes the synthesis, dispersion and encapsulation of a graft copolymer with nonionic, hydrophilic arms, and a hydrophobic backbone containing a glycidyl methacrylate functional group.
- This is an example of an encapsulation reaction using a different type of crosslinker.
- Nonionic, hydrophilic arms are necessary because the glycidyl methacrylate group would react with the acid groups found in the hydrophilic arms of Example 1.
- Portion 1 was heated to reflux temperature over a period of approximately 20 minutes. Portions 2 and 3 were added simultaneously to the reaction vessel while maintaining a reflux in the reaction vessel. Portion 2 was added over 180 minutes, and Portion 3 was added over 240 minutes. After the additions of Portions 2 and 3 were completed, Portion 4 was thoroughly mixed and added to the reaction vessel over 15 minutes, maintaining the reflux temperature. After the addition of Portion 4 was completed, the reaction mixture was maintained at reflux for 120 minutes and then cooled to room temperature.
- the resulting graft copolymer solution had a solids content of approximately 41% by weight and had the following overall approximate composition: 30% n-butyl acrylate; 20%> gylcidyl methacrylate; and 50% bisomer S20W.
- This material had a weight average molecular weight of about 24000 and a number average molecular weight of approximately 9000.
- a waterborne pigment dispersion was prepared by charging the following constituents into an 01 -Attritor media mill.
- the graft copolymer is mixed with deionized water to form Portion 1 (no neutralizing agent is needed).
- the material from Portion 1 was mixed with the materials in Portion 2 and the constituents were ground for 16 hours at 500 ⁇ m in an 01 -Attritor at 100°F.
- a uniform, transparent, waterborne pigment dispersion was formed that was stable and deflocculated and had a pH range of 2-4. This dispersion contains 15% pigment and 10% polymer.
- This material was then encapsulated by a crosslinking reaction between epoxide groups in the backbone and a hydrophobic diamine/catalyst system.
- Example 1 The above constituents mixed together and heated at 40-50°C, with efficient stirring, for a period of 6 hours. After this time period, the mixture is cooled to room temperature and tested for flocculation stability as in previous examples. The encapsulated samples were tested as in Example 1 and were more stable than the non-encapsulated samples.
- Two inks were prepared from unencapsulated and encapsulated dispersions and a third ink was prepared from a conventional dispersion to test the stability to thermal cycling achieved with the encapsulated dispersion as well as printability in an ink jet printing device.
- Dispersion #1 contains a quinacridone magenta pigment and a dispersant of the type prepared in Example 1 , the dispersion was prepared using a two roll mill process and was let down into water to 15%> by weight pigment and 2.5 parts pigment to 1 part dispersant.
- Dispersion #2 is dispersion #1 encapsulated using the process described in Example 1.
- Dispersion #3 uses a conventional methacrylic dispersant and a quniacridone magenta pigment and was prepared using a two roll mill process and was let down into water to 15%> pigment and 1.5 parts pigment to 1 part dispersant.
- Vehicle #1 contains 100 grams of an ethoxylated glycerol, 100 grams of 1,2 hexane diol, 100 grams of diethylene glycol, 27 grams of sodium dioctyl sulfosuccinate and the balance water to a total weight of 1000 grams.
- Ink #1 was prepared by adding 11 grams of dispersion #1, 25 grams of vehicle #1 and the balance water to a total of 50 grams.
- Ink #2 was prepared by adding 11 grams of dispersion #2, 25 grams of vehicle #1 and the balance water to a total of 50 grams.
- Ink #3 was prepared by adding 11 grams of dispersion #3, 25 grams of vehicle #1 and the balance water to a total of 50 grams.
- the inks were then tested in an ink jet printer and all printed well.
- the inks were also subjected to four freeze - thaw cycles from -20°C to 60°C and the change in particle size was observed. While all inks showed an increase in average particle size, the encapsulated sample (Ink #2) increased in size by about 25%> versus the 187%) increase for Ink #1 and 132% increase for Ink #3. This data indicates that Ink#2 would is more stable to thermal cycling.
- a tint suitable for use in manufacture of paint was prepared to demonstrate the utility of the present invention in such a process.
- a dispersion containing copper phthalocyanine blue pigment was prepared, ground and encapsulated.
- the resulting dispersion was then adjusted to a pH of 9 and the appearance of the dispersion drawdown (i.e., color and haze), and the percentage of solids, were compared to a standard sample.
- the dispersion Following the standardization of the dispersion, it was mixed with a base coat latex, water, a thickener and a biocide. The final solution pH, tinting strength and viscosity were monitored and additional water and/or thickener added to maintain standard viscosity and tint strength.
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- Chemical Kinetics & Catalysis (AREA)
- Dispersion Chemistry (AREA)
- Engineering & Computer Science (AREA)
- Materials Engineering (AREA)
- Wood Science & Technology (AREA)
- Life Sciences & Earth Sciences (AREA)
- Health & Medical Sciences (AREA)
- Medicinal Chemistry (AREA)
- Polymers & Plastics (AREA)
- Pigments, Carbon Blacks, Or Wood Stains (AREA)
- Inks, Pencil-Leads, Or Crayons (AREA)
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Abstract
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DE69916094.4T DE69916094T3 (de) | 1998-10-06 | 1999-10-05 | Dispersionen mit verbesserter stabilität |
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US10319498P | 1998-10-06 | 1998-10-06 | |
US103194P | 1998-10-06 | ||
PCT/US1999/023193 WO2000020520A1 (fr) | 1998-10-06 | 1999-10-05 | Dispersions a stabilite amelioree |
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EP (1) | EP1123358B2 (fr) |
JP (1) | JP3631140B2 (fr) |
KR (1) | KR100453307B1 (fr) |
CN (1) | CN1243801C (fr) |
AU (1) | AU755162B2 (fr) |
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WO2008043984A1 (fr) | 2006-10-11 | 2008-04-17 | Fujifilm Imaging Colorants Limited | Procédé, composition et encre |
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- 1999-10-05 AU AU62901/99A patent/AU755162B2/en not_active Ceased
- 1999-10-05 DE DE69916094.4T patent/DE69916094T3/de not_active Expired - Lifetime
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Also Published As
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CA2341977C (fr) | 2005-12-13 |
EP1123358B1 (fr) | 2004-03-31 |
JP3631140B2 (ja) | 2005-03-23 |
KR100453307B1 (ko) | 2004-10-20 |
AU6290199A (en) | 2000-04-26 |
EP1123358B2 (fr) | 2014-05-21 |
JP2002526259A (ja) | 2002-08-20 |
AU755162B2 (en) | 2002-12-05 |
KR20010080020A (ko) | 2001-08-22 |
WO2000020520A1 (fr) | 2000-04-13 |
US6262152B1 (en) | 2001-07-17 |
CN1243801C (zh) | 2006-03-01 |
DE69916094D1 (de) | 2004-05-06 |
DE69916094T2 (de) | 2004-10-28 |
DE69916094T3 (de) | 2014-10-09 |
CN1322228A (zh) | 2001-11-14 |
CA2341977A1 (fr) | 2000-04-13 |
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